The missing crystal structure in the series of N,N′,N′′-tris­(pyridinyl)benzene-1,3,5-tricarbox­amides: the 2-pyridinyl derivative

In the first reported crystal structure involving the potential ligand N,N′,N′′-tris­(2-pyridin­yl)-1,3,5-benzene­tricarboxamide, inter­molecular N—H...O hydrogen bonds link the mol­ecules via their amide groups into slanted ladder-like chains. Only two of the three amide groups in the mol­ecule are involved in hydrogen bonding, which influences the degree of out-of-plane twisting at each amide group.

Key indicators

• Single-crystal X-ray study
• T = 160 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.031
• wR factor = 0.088
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor       N1       --H1       .     Please Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         32 Report

Alert level G
PLAT142_ALERT_4_G s.u. on b - Axis Small or Missing ..............    0.00010 Ang.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         84 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         16 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2017); cell refinement: CrysAlis PRO (Rigaku OD, 2017); data reduction: CrysAlis PRO (Rigaku OD, 2017); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009), Mercury (Macrae et al., 2020); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b) and PLATON (Spek, 2015, 2020).

N,N',N''-Tris(pyridinyl)benzene-1,3,5-tricarboxamide

Crystal data

C24H18N6O3	F(000) = 912
Mr = 438.44	Dx = 1.437 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 8.2807 (1) Å	Cell parameters from 12896 reflections
b = 14.1554 (1) Å	θ = 3.1–74.1°
c = 17.5020 (2) Å	µ = 0.81 mm^−1
β = 98.920 (1)°	T = 160 K
V = 2026.71 (4) Å^3	Prism, pale yellow
Z = 4	0.24 × 0.09 × 0.09 mm

Data collection

Oxford Diffraction SuperNova, dual radiation diffractometer	4020 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray source	3786 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.018
Detector resolution: 10.3801 pixels mm^-1	θmax = 74.2°, θmin = 4.0°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2017)	k = −17→17
Tmin = 0.898, Tmax = 1.000	l = −21→18
19285 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.0474P)^2 + 0.5699P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
4020 reflections	Δρmax = 0.27 e Å^−3
311 parameters	Δρmin = −0.17 e Å^−3
0 restraints	Extinction correction: SHELXL-2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: dual	Extinction coefficient: 0.0012 (2)

Special details

Experimental. Data collection and full structure determination done by Prof. Anthony Linden: [e-mail]

Solvent used: methanol Cooling Device: Oxford Instruments Cryojet XL Crystal mount: on a glass fibre Frames collected: 1718 Seconds exposure per frame: 1.0-5.0 Degrees rotation per frame: 1.0 Crystal-detector distance (mm): 55.0 Client: Levi Senior Sample code: LS002

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.36342 (11)	0.88417 (6)	0.60262 (5)	0.0380 (2)
O2	0.64957 (8)	0.57226 (5)	0.62868 (4)	0.02469 (18)
O3	−0.13032 (8)	0.61942 (5)	0.39693 (4)	0.02547 (18)
N1	0.22689 (12)	0.90845 (6)	0.48097 (6)	0.0286 (2)
H1	0.1826 (19)	0.8797 (11)	0.4388 (9)	0.044 (4)*
N2	0.47719 (10)	0.44612 (6)	0.62364 (5)	0.02113 (19)
H2	0.3752 (17)	0.4245 (10)	0.6088 (8)	0.034 (4)*
N3	0.02167 (10)	0.49006 (6)	0.37699 (5)	0.02058 (19)
H3	0.1165 (18)	0.4642 (10)	0.3849 (8)	0.033 (4)*
N4	0.12823 (13)	1.03623 (7)	0.41011 (6)	0.0330 (2)
N5	0.53774 (11)	0.28992 (6)	0.64545 (6)	0.0271 (2)
N6	−0.07968 (11)	0.34722 (6)	0.32839 (5)	0.0249 (2)
C1	0.27688 (12)	0.74907 (7)	0.52677 (6)	0.0211 (2)
C2	0.39380 (12)	0.69079 (7)	0.56837 (6)	0.0208 (2)
H201	0.481926	0.717841	0.602596	0.025*
C3	0.38289 (11)	0.59313 (7)	0.56032 (5)	0.0185 (2)
C4	0.25660 (11)	0.55341 (7)	0.50819 (6)	0.0183 (2)
H4	0.249923	0.486807	0.501836	0.022*
C5	0.14014 (11)	0.61163 (7)	0.46542 (6)	0.0187 (2)
C6	0.14907 (12)	0.70904 (7)	0.47598 (6)	0.0205 (2)
H6	0.067381	0.748521	0.448346	0.025*
C7	0.29370 (12)	0.85343 (7)	0.54121 (6)	0.0245 (2)
C8	0.21855 (13)	1.00767 (7)	0.47569 (6)	0.0250 (2)
C9	0.29662 (15)	1.06853 (8)	0.53146 (7)	0.0338 (3)
H9	0.360791	1.045229	0.577297	0.041*
C10	0.27774 (16)	1.16473 (8)	0.51797 (8)	0.0375 (3)
H10	0.329125	1.208782	0.554908	0.045*
C11	0.18406 (15)	1.19619 (8)	0.45073 (7)	0.0335 (3)
H11	0.169393	1.261778	0.440413	0.040*
C12	0.11257 (15)	1.12956 (8)	0.39909 (7)	0.0351 (3)
H12	0.048082	1.151096	0.352713	0.042*
C13	0.51468 (11)	0.53603 (7)	0.60758 (6)	0.0189 (2)
C14	0.58508 (12)	0.37816 (7)	0.66292 (6)	0.0213 (2)
C15	0.72325 (13)	0.40119 (8)	0.71560 (6)	0.0278 (2)
H15	0.750539	0.465105	0.728164	0.033*
C16	0.81959 (14)	0.32752 (9)	0.74906 (7)	0.0354 (3)
H16	0.916222	0.340277	0.784429	0.043*
C17	0.77409 (14)	0.23553 (9)	0.73062 (7)	0.0367 (3)
H17	0.839025	0.184035	0.752419	0.044*
C18	0.63199 (14)	0.22034 (8)	0.67976 (7)	0.0331 (3)
H18	0.599003	0.156956	0.668379	0.040*
C19	−0.00171 (11)	0.57413 (7)	0.40961 (6)	0.0194 (2)
C20	−0.09362 (11)	0.44064 (7)	0.32296 (6)	0.0201 (2)
C21	−0.20550 (13)	0.48708 (8)	0.26842 (6)	0.0284 (2)
H21	−0.208759	0.554101	0.265813	0.034*
C22	−0.31225 (14)	0.43239 (9)	0.21791 (7)	0.0352 (3)
H22	−0.391456	0.461449	0.180111	0.042*
C23	−0.30220 (14)	0.33527 (9)	0.22314 (7)	0.0338 (3)
H23	−0.374646	0.296219	0.189504	0.041*
C24	−0.18422 (14)	0.29632 (8)	0.27848 (7)	0.0301 (2)
H24	−0.176591	0.229419	0.281387	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0526 (5)	0.0223 (4)	0.0315 (5)	0.0017 (3)	−0.0178 (4)	−0.0036 (3)
O2	0.0165 (3)	0.0221 (4)	0.0330 (4)	0.0004 (3)	−0.0039 (3)	−0.0040 (3)
O3	0.0167 (3)	0.0225 (4)	0.0345 (4)	0.0024 (3)	−0.0045 (3)	−0.0016 (3)
N1	0.0375 (5)	0.0185 (4)	0.0254 (5)	−0.0017 (4)	−0.0088 (4)	−0.0016 (4)
N2	0.0151 (4)	0.0218 (4)	0.0246 (4)	0.0011 (3)	−0.0029 (3)	0.0014 (3)
N3	0.0142 (4)	0.0212 (4)	0.0243 (4)	0.0006 (3)	−0.0033 (3)	−0.0009 (3)
N4	0.0390 (5)	0.0252 (5)	0.0306 (5)	0.0004 (4)	−0.0080 (4)	0.0027 (4)
N5	0.0246 (4)	0.0237 (5)	0.0316 (5)	0.0024 (3)	0.0002 (4)	0.0032 (4)
N6	0.0235 (4)	0.0226 (4)	0.0269 (5)	−0.0015 (3)	−0.0011 (3)	−0.0019 (3)
C1	0.0214 (5)	0.0191 (5)	0.0220 (5)	−0.0002 (4)	0.0010 (4)	−0.0009 (4)
C2	0.0187 (4)	0.0217 (5)	0.0211 (5)	−0.0012 (4)	−0.0002 (4)	−0.0021 (4)
C3	0.0157 (4)	0.0208 (5)	0.0184 (5)	0.0016 (4)	0.0011 (3)	−0.0003 (4)
C4	0.0167 (4)	0.0181 (4)	0.0198 (5)	−0.0003 (3)	0.0017 (4)	−0.0006 (4)
C5	0.0152 (4)	0.0209 (5)	0.0194 (5)	−0.0008 (3)	0.0007 (4)	0.0002 (4)
C6	0.0187 (4)	0.0200 (5)	0.0217 (5)	0.0020 (4)	−0.0002 (4)	0.0016 (4)
C7	0.0250 (5)	0.0203 (5)	0.0260 (5)	0.0008 (4)	−0.0033 (4)	−0.0013 (4)
C8	0.0264 (5)	0.0199 (5)	0.0271 (5)	−0.0004 (4)	−0.0010 (4)	0.0007 (4)
C9	0.0409 (6)	0.0229 (5)	0.0330 (6)	−0.0010 (5)	−0.0090 (5)	−0.0006 (4)
C10	0.0456 (7)	0.0224 (6)	0.0411 (7)	−0.0032 (5)	−0.0042 (5)	−0.0048 (5)
C11	0.0385 (6)	0.0201 (5)	0.0419 (7)	0.0033 (4)	0.0064 (5)	0.0044 (5)
C12	0.0399 (6)	0.0283 (6)	0.0344 (6)	0.0050 (5)	−0.0032 (5)	0.0074 (5)
C13	0.0166 (4)	0.0206 (5)	0.0185 (5)	0.0022 (3)	0.0000 (3)	−0.0039 (4)
C14	0.0181 (5)	0.0244 (5)	0.0209 (5)	0.0025 (4)	0.0020 (4)	0.0033 (4)
C15	0.0242 (5)	0.0328 (6)	0.0241 (5)	−0.0008 (4)	−0.0033 (4)	0.0053 (4)
C16	0.0256 (5)	0.0469 (7)	0.0305 (6)	0.0014 (5)	−0.0057 (4)	0.0143 (5)
C17	0.0303 (6)	0.0399 (7)	0.0389 (7)	0.0108 (5)	0.0025 (5)	0.0185 (5)
C18	0.0327 (6)	0.0260 (6)	0.0402 (7)	0.0056 (5)	0.0042 (5)	0.0082 (5)
C19	0.0162 (4)	0.0198 (5)	0.0210 (5)	−0.0014 (3)	−0.0006 (4)	0.0031 (4)
C20	0.0159 (4)	0.0234 (5)	0.0203 (5)	−0.0013 (4)	0.0007 (4)	−0.0011 (4)
C21	0.0283 (5)	0.0277 (5)	0.0262 (6)	0.0026 (4)	−0.0049 (4)	0.0005 (4)
C22	0.0298 (6)	0.0438 (7)	0.0272 (6)	0.0041 (5)	−0.0103 (5)	−0.0030 (5)
C23	0.0266 (5)	0.0411 (7)	0.0310 (6)	−0.0065 (5)	−0.0039 (4)	−0.0110 (5)
C24	0.0296 (5)	0.0261 (5)	0.0332 (6)	−0.0054 (4)	0.0005 (4)	−0.0064 (4)

Geometric parameters (Å, º)

O1—C7	1.2189 (13)	C5—C6	1.3916 (13)
O2—C13	1.2325 (12)	C5—C19	1.5032 (13)
O3—C19	1.2334 (12)	C6—H6	0.9500
N1—C7	1.3578 (14)	C8—C9	1.3846 (15)
N1—C8	1.4085 (14)	C9—C10	1.3867 (16)
N1—H1	0.872 (16)	C9—H9	0.9500
N2—C13	1.3499 (13)	C10—C11	1.3792 (18)
N2—C14	1.4163 (12)	C10—H10	0.9500
N2—H2	0.898 (14)	C11—C12	1.3751 (17)
N3—C19	1.3468 (13)	C11—H11	0.9500
N3—C20	1.4195 (12)	C12—H12	0.9500
N3—H3	0.857 (14)	C14—C15	1.3923 (14)
N4—C8	1.3319 (14)	C15—C16	1.3864 (16)
N4—C12	1.3384 (15)	C15—H15	0.9500
N5—C14	1.3304 (14)	C16—C17	1.3798 (19)
N5—C18	1.3395 (14)	C16—H16	0.9500
N6—C20	1.3295 (14)	C17—C18	1.3778 (18)
N6—C24	1.3406 (14)	C17—H17	0.9500
C1—C2	1.3890 (14)	C18—H18	0.9500
C1—C6	1.3927 (13)	C20—C21	1.3883 (14)
C1—C7	1.5015 (14)	C21—C22	1.3855 (16)
C2—C3	1.3910 (14)	C21—H21	0.9500
C2—H201	0.9500	C22—C23	1.3795 (18)
C3—C4	1.3951 (13)	C22—H22	0.9500
C3—C13	1.4996 (13)	C23—C24	1.3795 (16)
C4—C5	1.3949 (13)	C23—H23	0.9500
C4—H4	0.9500	C24—H24	0.9500
C7—N1—C8	129.27 (9)	C12—C11—C10	117.85 (11)
C7—N1—H1	117.2 (10)	C12—C11—H11	121.1
C8—N1—H1	113.5 (10)	C10—C11—H11	121.1
C13—N2—C14	126.40 (8)	N4—C12—C11	124.06 (11)
C13—N2—H2	119.8 (9)	N4—C12—H12	118.0
C14—N2—H2	113.8 (9)	C11—C12—H12	118.0
C19—N3—C20	126.29 (8)	O2—C13—N2	123.84 (9)
C19—N3—H3	119.8 (9)	O2—C13—C3	119.29 (9)
C20—N3—H3	113.7 (9)	N2—C13—C3	116.86 (8)
C8—N4—C12	116.92 (10)	N5—C14—C15	123.69 (10)
C14—N5—C18	117.19 (10)	N5—C14—N2	112.64 (9)
C20—N6—C24	116.60 (9)	C15—C14—N2	123.65 (10)
C2—C1—C6	119.46 (9)	C16—C15—C14	117.61 (11)
C2—C1—C7	117.21 (9)	C16—C15—H15	121.2
C6—C1—C7	123.31 (9)	C14—C15—H15	121.2
C1—C2—C3	120.54 (9)	C17—C16—C15	119.52 (11)
C1—C2—H201	119.7	C17—C16—H16	120.2
C3—C2—H201	119.7	C15—C16—H16	120.2
C2—C3—C4	119.81 (9)	C18—C17—C16	118.25 (11)
C2—C3—C13	116.71 (8)	C18—C17—H17	120.9
C4—C3—C13	123.44 (9)	C16—C17—H17	120.9
C5—C4—C3	119.91 (9)	N5—C18—C17	123.69 (11)
C5—C4—H4	120.0	N5—C18—H18	118.2
C3—C4—H4	120.0	C17—C18—H18	118.2
C6—C5—C4	119.73 (9)	O3—C19—N3	124.04 (9)
C6—C5—C19	117.15 (8)	O3—C19—C5	119.95 (9)
C4—C5—C19	123.07 (9)	N3—C19—C5	116.00 (8)
C5—C6—C1	120.49 (9)	N6—C20—C21	124.15 (9)
C5—C6—H6	119.8	N6—C20—N3	113.61 (9)
C1—C6—H6	119.8	C21—C20—N3	122.20 (9)
O1—C7—N1	124.07 (10)	C22—C21—C20	117.76 (11)
O1—C7—C1	121.24 (9)	C22—C21—H21	121.1
N1—C7—C1	114.69 (9)	C20—C21—H21	121.1
N4—C8—C9	123.85 (10)	C23—C22—C21	119.24 (11)
N4—C8—N1	111.99 (9)	C23—C22—H22	120.4
C9—C8—N1	124.15 (10)	C21—C22—H22	120.4
C8—C9—C10	117.58 (11)	C24—C23—C22	118.28 (10)
C8—C9—H9	121.2	C24—C23—H23	120.9
C10—C9—H9	121.2	C22—C23—H23	120.9
C11—C10—C9	119.74 (11)	N6—C24—C23	123.93 (11)
C11—C10—H10	120.1	N6—C24—H24	118.0
C9—C10—H10	120.1	C23—C24—H24	118.0
C6—C1—C2—C3	−0.78 (15)	C2—C3—C13—O2	−25.12 (13)
C7—C1—C2—C3	177.55 (9)	C4—C3—C13—O2	152.69 (9)
C1—C2—C3—C4	2.12 (14)	C2—C3—C13—N2	155.68 (9)
C1—C2—C3—C13	−179.99 (9)	N2—C13—C3—C4	−26.51 (13)
C2—C3—C4—C5	−1.17 (14)	C18—N5—C14—C15	−1.58 (16)
C13—C3—C4—C5	−178.92 (9)	C18—N5—C14—N2	−179.99 (9)
C3—C4—C5—C6	−1.09 (14)	C13—N2—C14—N5	−155.86 (10)
C3—C4—C5—C19	−178.46 (9)	C13—N2—C14—C15	25.72 (15)
C4—C5—C6—C1	2.44 (14)	N5—C14—C15—C16	2.67 (16)
C19—C5—C6—C1	179.97 (9)	N2—C14—C15—C16	−179.09 (10)
C2—C1—C6—C5	−1.51 (15)	C14—C15—C16—C17	−1.39 (17)
C7—C1—C6—C5	−179.73 (9)	C15—C16—C17—C18	−0.75 (18)
C8—N1—C7—O1	−1.7 (2)	C14—N5—C18—C17	−0.81 (17)
C8—N1—C7—C1	178.72 (10)	C16—C17—C18—N5	1.96 (19)
C2—C1—C7—O1	−25.98 (15)	C20—N3—C19—O3	0.87 (16)
C6—C1—C7—O1	152.27 (11)	C20—N3—C19—C5	179.93 (9)
C2—C1—C7—N1	153.59 (10)	C6—C5—C19—O3	−26.11 (13)
N1—C7—C1—C6	−28.16 (15)	C4—C5—C19—O3	151.33 (10)
C12—N4—C8—C9	−0.62 (18)	C6—C5—C19—N3	154.80 (9)
C12—N4—C8—N1	−179.82 (11)	N3—C19—C5—C4	−27.77 (13)
C7—N1—C8—N4	−173.33 (11)	C24—N6—C20—C21	−1.56 (15)
C7—N1—C8—C9	7.5 (2)	C24—N6—C20—N3	−179.45 (9)
N4—C8—C9—C10	0.56 (19)	C19—N3—C20—N6	−148.25 (10)
N1—C8—C9—C10	179.66 (11)	C19—N3—C20—C21	33.81 (15)
C8—C9—C10—C11	−0.2 (2)	N6—C20—C21—C22	1.87 (16)
C9—C10—C11—C12	−0.1 (2)	N3—C20—C21—C22	179.58 (10)
C8—N4—C12—C11	0.30 (19)	C20—C21—C22—C23	−0.70 (17)
C10—C11—C12—N4	0.1 (2)	C21—C22—C23—C24	−0.59 (18)
C14—N2—C13—O2	−3.35 (16)	C20—N6—C24—C23	0.12 (16)
C14—N2—C13—C3	175.81 (9)	C22—C23—C24—N6	0.93 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3^i	0.898 (14)	2.108 (14)	2.9866 (11)	165.6 (13)
N3—H3···O2^ii	0.857 (14)	2.054 (14)	2.8781 (11)	160.9 (13)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1.